Peter Thiel is an iconoclastic billionaire venture capitalist who generally defies convention. He made his first millions at PayPal. He was the first outside investor in Facebook. He’s a delegate for Republican presidential candidate Donald Trump, an almost unfathomable affiliation in Silicon Valley, and an avowed libertarian who once suggested that women’s suffrage was bad for democracy. Thiel emphatically exclaimed “I am proud to be gay” at last month’s Republican National Convention, in Cleveland. Thiel has also been surreptitiously underwriting a series of lawsuits—most notably, Hulk Hogan’s (née Terry Bollea) $140 million defamation case—against Gawker, the site that outed him in a 2007 blog post.

On Tuesday, after months of anticipation, the media company—fiercely independent since its 2002 founding—officially inaugurated its auction process. Thiel noted the occasion with an op-ed in The New York Times. “I am proud to have contributed financial support to [Bollea’s] case,” he wrote in an article published Monday evening, an hour before the Gawker bids were due. “I will support him until his final victory—Gawker said it intends to appeal—and I would gladly support someone else in the same position.”

By Tuesday evening, Univision had outbid Ziff Davis to take control of the blog network. New York Magazine, Penske Media, and Vox Media, which were all floated as potential acquirers, did not end up submitting bids. Gawker Media was once valued at as much as $250 million, before Hogan’s lawsuit. Univision picked it up for $135 million.

Thiel has only recently embraced his role as Gawker's nemesis. Until May 2016, when a Forbes article identified him as the shadowy benefactor partly funding Bollea’s lawsuit, he remained silent about his involvement. Thiel has also not disclosed whether he is supporting myriad other suits against the company and some of its former journalists. But his op-ed demonstrated the precarious and ever-shifting lines in terms of how privacy is viewed in the digital age. “All people deserve respect, and nobody’s sexuality should be made a public fixation,” Thiel wrote. At the same time, the 48-year-old venture capitalist is a board member at Facebook and a co-founder of the C.I.A.-backed Palantir, both multi-billion-dollar companies that collect data about their users, or their clients’ users, and monetize their personal information.

The Bollea saga has, in some ways, been just as precarious for journalists, some of whom disagreed with Gawker’s news judgment as much as they despised Thiel’s participation in its financial demise. In his opinion piece, Thiel argued that journalists have nothing to fear from him, but he also has set a dangerous precedent for media companies who dare to critique wealthy, powerful individuals like himself. “A free press is vital for public debate. Since sensitive information can sometimes be publicly relevant, exercising judgment is always part of the journalist’s profession,” he wrote. “It’s not for me to draw the line, but journalists should condemn those who willfully cross it.” Both Gawker founder Nick Denton and former Gawker.com editor-in-chief A.J. Daulerio now face personal bankruptcy as the result of the Hogan lawsuit.

It’s the end of an era—and not simply for Gawker. When the site was born, its gleefully caustic voice and acidic humor (invariably described as “snarky” at the time) represented an important counterbalance to the cautious conformism of so much establishment journalism. The economy and culture were changing rapidly, perhaps far more rapidly than many at the time appreciated, and Gawker often seemed to sense the shift earlier than most, calling out behavior that its writers considered antithetical to today’s transparent, tech-driven era.

But like other formerly independent Web pioneers, such as The Huffington Post and Yahoo, Gawker struggled to take full advantage of subsequent shifts. In recent years, Gawker.com left behind its media-mocking roots to embrace general-interest news, even as the rest of the Internet seemed to drive toward ever greater specificity. (The site's pivot to politics last year looked like a late, and half-hearted, attempt to acknowledge this trend.) And though it touts its proprietary commenting community, Kinja, Gawker Media never became a true hub for innovation during its 14-year run. It did not evolve into a pioneer in video or other forms of storytelling. Instead it remained Gawker, even as that identity became less and less clear. Meanwhile, the business suffered from the company's difficulty in selling advertising against its content. In many ways, it is hardly a surprise that this once fearsome outsider has now joined Yahoo and the HuffPost as a member of a multi-national media conglomerate.

Perhaps more notably, Gawker’s editorial instinct never quite seemed to mature with its audience. In an interview last month, New Yorker editor-in-chief David Remnick pressed Denton on his editorial motivation for outing a subject, such as Thiel. “Who should do the coming out?” Remnick asked. Denton’s answer was both poignant and yet seemingly aloof. “It’s part of somebody’s biography,” he replied. “And I think the world is a lot healthier with Silicon Valley’s most successful venture capitalist being gay and known to be gay. . . . And for it to be clear to gay people growing up that there are other paths than becoming a hairdresser or fashion designer.”

That may be the case, but it may not be Gawker’s responsibility, either. The Web has changed in the past decade, like any industry, and become a more regulated and sophisticated environment, far different from the Wild West that Gawker operated in during its earliest days. (Even Denton himself seemed to recognize this when he promised last year to make the site “20 percent nicer”.) Gawker, in some ways, is responsible for that shift. Legions of the site's staff and former writers gathered to bid adieu to its independence last week at the Gawker Media offices in the Flatiron District. They were there to turn the page on Gawker. Many, you can be certain, had already done so long ago.